Bianca Bova is a cultural critic who writes about contemporary art. An art critic writing about late night television? Yes. In her LateNighter debut, she looks at one of our very favorite classic episodes of Late Night with David Letterman.
On a Thursday night in October of 1987, David Letterman checked into a suite on the twenty-sixth floor of the Milford Plaza Hotel. Situated on 8th Avenue between West 44th and West 45th Streets, the hotel sat on the edge of a Times Square that was then still home to “the sleaziest block in America.”
The broadcast begins with a grinning Letterman, looking trim in a double breasted navy sport coat, striped shirt, silk tie, white tube socks, chinos, and a pair of Adidas Hercules boxing boots, standing against the backdrop of the hotel hallway’s lurid silver lamé wallpaper. His introduction is brief, supplying no explanation for the show’s locale beyond the acknowledgement of a supposed white lie he’s told NBC that sufficed “to get the money so we could come over here and screw around for an hour.” This is followed by the short, deadpan laugh—as obfuscating as it is alarming—that is Letterman’s signature.
The suite Letterman has commandeered for the evening is a penthouse named for Broadway legend Helen Hayes, who it seems safe to say likely never stepped foot on the premises in the years the hotel operated as the Milford Plaza. Crammed into the suite’s sitting room is Late Night’s house band led by Paul Shaffer, and a production crew of roughly a dozen, who spill over into the bedroom-turned-control room in which it is predicted “at least one accidental death will occur tonight.”
Letterman reels around the room, pointing out fire code violations, making quips about visits from the vice squad, threatening to call in the house dick, and making asides about room rental by the hour, before approaching the door to the closet that’s serving as a makeshift green room this night.
Nervousness flashes across his face as he attempts to pull open the door only to be met by the resistance of someone on the other side holding it shut. When the door is finally released, sending the host back on his heels, it opens to reveal, sitting shoulder-to-shoulder below a shelf of blankets and spare towels, the evening’s three guests: singer Carly Simon, podiatrist and shoe collector Dr. Ted Burgeas, and writer Hunter S. Thompson.
Hauling the production of Late Night with David Letterman, then in its sixth season, half a dozen blocks to the Milford Plaza Hotel was by no means the most radical way in which Letterman (and the staff whom he’s credited as essential to shaping the show’s identity) manipulated the standard talk show format. It is, however, in some ways the strangest.
The Milford Plaza Hotel opened its doors in 1928 as the Hotel Lincoln. It changed hands over the years, until in 1980, under the ownership of storied hoteliers the Milstein family, it was newly christened as The Milford Plaza. Its 1,310 rooms were designed by the esteemed hotel decorator Marilynn Motto, who was quoted in a 1962 interview with the New York Times saying, “You live in a hotel tentatively—a day, a week or a month…Travelers often expect a little excitement in the decoration of hotel rooms. Many seem to thrive on bright colors as long as the palette avoids the garish.”
This aversion to the garish seemed to have left Motto by the time she selected the allover-patterned curtains and Michel Delacroix prints that adorn the walls of the Helen Hayes Suite. The tentativeness of hotel life, however, endures, and Letterman was not a stranger to it. In a 1980 interview with Tom Snyder on the Tomorrow show, Letterman, discussing his initial difficulty adapting to city life, noted “When I first moved to New York City I was living at 55th and 6th Avenue…it’s the busiest, loudest, nastiest intersection in the world.”
The decidedly commercial intersection in Midtown seems a strange place to have taken up residence, and indeed, it begot rumors that would follow Letterman for years to come. To wit, actress Terri Garr, a frequent guest on Late Night, once asked if he was living in a sensory deprivation tank in a facility in Midtown—specifically, in the 50’s—claiming to have been told so by a realtor. In reality Letterman had been living in a hotel, something he confirmed when speaking to Jane Pauly during a segment on the Today show, “I don’t have a house to live in,” he noted, “I’m living in a hotel, in which I’m the only person not from Argentina…I feel very left out, but that’s where I’m presently making my home.”
The Shoreham Hotel, which by all accounts seems to have been Letterman’s residence in those years, still sits at 33 W. 55th Street. Built in the 1930s, it had long been in decline by the time he would have moved in.
“At one time it had catered to a wealthy South American clientele,” its former proprietor Bernard Goldberg said in a 2005 New York Times article about the hotel, “but no one had invested any money in it for a long time, and it had grown seedy.”
The decision to produce a program from the Milford Plaza, then, takes on a different tone. It is not like Fish Cleaning Night or Duplicate Key Night—other Letterman theme shows of the era—an instance of deliberately manufactured novelty for novelty’s sake. It is Letterman at his most acuminous, a strange individual at home in strange environs, capable of articulating a highly specific atmosphere not because of his general canniness, but because he was seemingly of it while everyone else present is merely in it. Spiritually speaking, less a guest than a resident; and in this way, the ideal host.
That beyond taking the Milford Plaza on as its temporary home, the program is not preoccupied with the hotel itself underscores this sense of possession on Letterman’s part. For the whole of the hour, the show never ventures beyond the 26th floor. Despite Letterman’s long history of engaging with strangers in man-on-the-street segments and remotes that took him everywhere from dentists’ offices to lampshade retailers, at the Milford Plaza Hotel he does not visit the lobby, the restaurant-lounge, or the bar. He does not go down to the sidewalk to catch the patrons or employees of the nearby Broadway or Triple-X theatres.
The only time after Letterman’s opening remarks that the production ventures out of the room at all is for a brief jaunt down the hallway to knock on doors in hopes of conscripting neighboring guests as a proxy-audience for the evening. The only respondent this search effort yields is John Godfrey, a man who seems cagey about everything from his name, to his job, to his purpose for visiting from Albany, New York. A better representative of hotel clientele could not be engineered.
Once settled back in the suite, Letterman addresses the chore of arranging for room service. The order he places is an appropriately grotesque assortment of cheeseburgers, steak sandwiches, cheese and crackers “for a hundred,” cappuccinos, and a case of the house brand scotch (“of course, the cheaper the better,” quips the concierge on the other end of the phone). The order is promised to arrive in “about five or ten minutes” which no one seems to take literally until a knock at the door an astonishingly short time later.
“Now, is that actually our order?…This looks like a dummy order. Was this stuff prepared now, or like earlier today?” Letterman asks of the bellman wheeling in a utility cart teeming with plates. The cheeseburgers are nearly raw. The steak sandwiches are nowhere to be found. There are several large salads no one can recall having ordered. The house scotch is Crown Sterling.
As the program prepares to break for commercial, Carly Simon, who gamely shares a couch with the mysterious Mr. Godfrey after having performed mid-way through the program, seems more buoyant than during her brief interview. She hams it up for the camera, showing off her plate of food as if it were a game show prize. Letterman sits in an adjacent reading chair, futilely attempting to peel layers of Saran wrap from an enormous plastic serving bowl filled to the brim with coleslaw.
On return, crowded around the couch on hanging racks and filling the gaps on the table between the plates of food are dozens of pairs of used shoes. It is Ted Burgeas’ collection. At the time of his appearance, Dr. Burgeas, a podiatrist hailing from Phoenix, Arizona, had been in New York for a week on Late Night’s dime, having been bumped from the program for several days in succession.
He had begun collecting the footwear of notable cultural figures for thirty years, after having been given a pair of ill-fated wedding shoes by his landlady, a jilted-bride. That Letterman unironically refers to his collecting habit as “a natural extension of your line of work” speaks either to his generosity in handling his more eccentric guests or to his own eccentricity; both are arguably, equally plausible. Still, the discussion of the collection does not progress beyond the first two pairs of shoes before Letterman breaks down.
“What is going on here? Just exactly what the hell are we doing here?” he cuts in to Dr. Burgeas’ discussion of the indication of a short metatarsal evident in the wear pattern on the soles of Barry Goldwater’s wingtips, “This guy’s talking about feet, we’re in a hotel room, we have bad room service food!”
“It finally dawned on you, just now!?” comes the voice of Paul Shaffer from off-camera, with seeming genuinity.
“Yes, now, in the middle of a discussion of a metatarsal!” comes the resigned response from Letterman.
Dr. Burgeas, undeterred, holds up the shoes of philanthropist Clement Stone, which he divulges have “a little lift” in them.
When the doctor has trotted out his last pair (though not before showing Loretta Young’s knee-high suede boots, soles still encrusted with mud and straw, eliciting a remark of “Jeez, you didn’t boil these things or anything!?” from Letterman, who immediately begins brushing imaginary dirt from his hands) he is bid farewell, the shoes are cleared from the camera’s view, and Hunter S. Thompson supplants him to the left of Simon.
What state Thompson is in is the educated guess of anyone who can triangulate his historic drinking habits and drug use with the program’s tape date. Within a matter of minutes, while mid-sentence, he begins wrestling off his overcoat. This sends his lavalier microphone flying and, despite the friendly assistance of a grinning Simon, Thompson still extends his arm to Letterman to pull him free of his left sleeve, a request met with ox-eyed exasperation.
“Hunter—let me ask you a question,” he says, “Why didn’t you take off your jacket before we started taping?”
“It’s cold behind me,” Thompson explains, gesturing to the open windows, and the white polyester under curtains sucked through the frames, twisting in the autumn wind, “and it’s hot here in front of me,” gesturing to the lights, “I wasn’t sure which was gonna prevail.”
From there the conversation takes an almost astonishingly earnest turn, delving into Thompson’s long history in politics, both as a reporter and candidate for office himself. By the time the discussion has turned to speculative questions of the upcoming presidential race, the camera has cut away to a crew member mid-yawn. At the behest of a producer, Letterman somewhat reluctantly ends the segment for time.
On return from the program’s final commercial break, holding up a placard from the lobby that bears the message “STAGE DOOR MIKE COSSI APPEARING NITELY NO COVER NO MINIMUM” Letterman introduces the program’s closing act: the hotel’s lounge singer, clad in a garment that can only be described as the lovechild of a dinner jacket and a chore coat. His rendition of Frank Sinatra’s “This Love of Mine,” made unbearably maudlin by the strained rasp of his voice, invites a desultory air to settle over the room as the end credits begin to roll.
“We did a show from the Milford Plaza Hotel,” Mary Connelly, a longtime Late Night producer recalled in an interview for Letterman’s YouTube channel. “I believe Dave, on seeing this hotel room, may have said, ‘If I was going to kill myself, this room wouldn’t talk me out of it.’”
Letterman has long proven himself singularly capable of tapping a particular and peculiar vein of the American culture. It is one that is full of easily exploitable kitsch on the surface, with a plaintively desperate interior life. He leads us where he knows it to live: in twenty-four hour donut shops; in automotive impound lots; and in The Milford Plaza Hotel. He addresses them skillfully, carefully, with candor wrapped in a good-mannered Midwestern politeness that is sweet, but nonetheless troubling. These are places, Letterman seems to suggest, that in order to fully experience the society of which you are a part, must be visited; but—and take it on his good authority—you wouldn’t want to live there.
With gratitude to Letterman archivist Don Giller, Late Night with David Letterman‘s Milford Plaza episode can be viewed in its entirety below:
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I don’t think Systems Consultant John Godfrey was mysterious at all. Remember, this was before the Internet. Most systems consultants at the time either worked on computers or telecommunications. They had to travel in person to provide their service to a client. He could also have been town for technical training. I was working as a systems engineer at the time. If I traveled, I had a meager allowance for meals. I would eat at local restaurants rather than in the mid-level hotels our corporate travel departments booked us into. Many times, consultants like John worked on projects that had a confidentiality clause written into the contract. Besides, they were not going to bore people by telling them they were on a project to convert BISYNC to SDLC or some other arcane job.